Organic molecules for use in optoelectronic devices

ABSTRACT

An organic molecule is disclosed having a structure of Formula I: 
     
       
         
         
             
             
         
       
     
     wherein
     X is O or S; Y is O or S;   R 1  is selected from the group consisting of:
       hydrogen,   deuterium,   C 1 -C 5 -alkyl,
           which is optionally substituted with one or more substituents R 5 ;   
           C 6 -C 60 -aryl,
           which is optionally substituted with one or more substituents R 5 ; and   
           C 3 -C 57 -heteroaryl,
 
which is optionally substituted with one or more substituents R 5 .

The invention relates to organic light-emitting molecules and their usein organic light-emitting diodes (OLEDs) and in other optoelectronicdevices.

DESCRIPTION

The object of the present invention is to provide molecules which aresuitable for use in optoelectronic devices.

This object is achieved by the invention which provides a new class oforganic molecules.

According to the invention the organic molecules are purely organicmolecules, i.e. they do not contain any metal ions in contrast to metalcomplexes known for use in optoelectronic devices.

According to the present invention, the organic molecules exhibitemission maxima in the blue, sky-blue or green spectral range. Theorganic molecules exhibit in particular emission maxima between 420 nmand 520 nm, preferably between 440 nm and 495 nm, more preferablybetween 450 nm and 470 nm. The photoluminescence quantum yields of theorganic molecules according to the invention are, in particular, 20% ormore. The use of the molecules according to the invention in anoptoelectronic device, for example an organic light-emitting diode(OLED), leads to higher efficiencies or higher color purity, expressedby the full width at half maximum (FWHM) of emission, of the device.Corresponding OLEDs have a higher stability than OLEDs with knownemitter materials and comparable color.

The organic light-emitting molecule of the invention comprises orconsists of a structure of Formula I,

X is O or S;

-   Y is O or S;-   R¹ is selected from the group consisting of:-   hydrogen,-   deuterium,-   C₁-C₅-alkyl,    -   which is optionally substituted with one or more substituents        R⁵;-   C₆-C₆₀-aryl,    -   which is optionally substituted with one or more substituents        R⁵; and-   C₃-C₅₇-heteroaryl,    -   which is optionally substituted with one or more substituents        R⁵.-   R², R³, and R⁴ is independently from each other selected from the    group consisting of:-   hydrogen,-   deuterium,-   C₁-C₄₀-alkyl,    -   which is optionally substituted with one or more substituents        R⁵;-   C₁-C₄₀-alkoxyl,    -   which is optionally substituted with one or more substituents        R⁵;-   C₂-C₄₀-alkenyl,    -   which is optionally substituted with one or more substituents        R⁵;-   C₂-C₄₀-alkynyl,    -   which is optionally substituted with one or more substituents        R⁵;-   C₆-C₆₀-aryl,    -   which is optionally substituted with one or more substituents        R⁵;-   C₃-C₅₇-heteroaryl,    -   which is optionally substituted with one or more substituents        R⁵;-   CN;-   CF₃;-   N(R⁵)₂;-   OR⁵, and-   Si(R⁵)₃.

R^(I), R^(II), R^(III), R^(IV), R^(V) and R^(VI) is independently fromeach other selected from the group consisting of:

-   hydrogen,-   deuterium,-   C₁-C₄₀-alkyl,    -   which is optionally substituted with one or more substituents        R⁵;-   C₁-C₄₀-alkoxyl,    -   which is optionally substituted with one or more substituents        R⁵;-   C₂-C₄₀-alkenyl,    -   which is optionally substituted with one or more substituents        R⁵;-   C₂-C₄₀-alkynyl,    -   which is optionally substituted with one or more substituents        R⁵;-   C₆-C₆₀-aryl,    -   which is optionally substituted with one or more substituents        R⁵;-   C₃-C₅₇-heteroaryl,    -   which is optionally substituted with one or more substituents        R⁵;-   CN;-   CF₃;-   N(R⁵)₂;-   OR⁵, and-   Si(R⁵)₃.

R⁵ is at each occurrence independently from another selected from thegroup consisting of:

-   hydrogen, deuterium, OPh, CF₃, CN, F,-   C₁-C₅-alkyl,    -   wherein optionally one or more hydrogen atoms are independently        from each other substituted by deuterium, CN, CF₃, or F;-   C₁-C₅-alkoxy,    -   wherein optionally one or more hydrogen atoms are independently        from each other substituted by deuterium, CN, CF₃, or F;-   C₁-C₅-thioalkoxy,    -   wherein optionally one or more hydrogen atoms are independently        from each other substituted by deuterium, CN, CF₃, or F;-   C₂-C₅-alkenyl,    -   wherein optionally one or more hydrogen atoms are independently        from each other substituted by deuterium, CN, CF₃, or F;-   C₂-C₅-alkynyl,    -   wherein optionally one or more hydrogen atoms are independently        from each other substituted by deuterium, CN, CF₃, or F;-   C₆-C₁₈-aryl,    -   which is optionally substituted with one or more C₁-C₅-alkyl        substituents;-   C₃-C₁₇-heteroaryl,    -   which is optionally substituted with one or more C₁-C₅-alkyl        substituents;-   N(C₆-C₁₈-aryl)₂,-   N(C₃-C₁₇-heteroaryl)₂; and-   N(C₃-C₁₇-heteroaryl) (C₆-C₁₈-aryl).

In a further embodiment of the invention, X and Y are the same, inparticular X and Y are each O.

In a further embodiment of the invention, R², R³ and R⁴ is independentlyfrom another selected from the group consisting of:

-   hydrogen,-   deuterium,-   halogen,-   Me,-   ^(i)Pr,-   ^(t)Bu,-   CN,-   CF₃,-   Ph, which is optionally substituted with one or more substituents    independently from each other selected from the group consisting of    Me, ^(i)Pr, ^(t)Bu, CN, CF₃, and Ph,-   pyridinyl, which is optionally substituted with one or more    substituents independently from each other selected from the group    consisting of Me, ^(i)Pr, ^(t)Bu, CN, CF₃, and Ph,-   pyrimidinyl, which is optionally substituted with one or more    substituents independently from each other selected from the group    consisting of Me, ^(i)Pr, ^(t)Bu, CN, CF₃, and Ph,-   carbazolyl, which is optionally substituted with one or more    substituents independently from each other selected from the group    consisting of Me, ^(i)Pr, ^(t)Bu, CN, CF₃, and Ph,-   triazinyl, which is optionally substituted with one or more    substituents independently from each other selected from the group    consisting of Me, ^(i)Pr, ^(t)Bu, CN, CF₃, and Ph,-   and N(Ph)₂.

In a further embodiment of the invention, R^(I), R^(II), R^(III),R^(IV), R^(V) and R^(VI) is independently from another selected from thegroup consisting of:

-   hydrogen,-   deuterium,-   halogen,-   Me,-   ^(i)Pr,-   ^(t)Bu,-   CN,-   CF₃,-   Ph, which is optionally substituted with one or more substituents    independently from each other selected from the group consisting of    Me, ^(i)Pr, ^(t)Bu, CN, CF₃, and Ph,-   pyridinyl, which is optionally substituted with one or more    substituents independently from each other selected from the group    consisting of Me, ^(i)Pr, ^(t)Bu, CN, CF₃, and Ph,-   pyrimidinyl, which is optionally substituted with one or more    substituents independently from each other selected from the group    consisting of Me, ^(i)Pr, ^(t)Bu, CN, CF₃, and Ph,-   carbazolyl, which is optionally substituted with one or more    substituents independently from each other selected from the group    consisting of Me, ^(i)Pr, ^(t)Bu, CN, CF₃, and Ph,-   triazinyl, which is optionally substituted with one or more    substituents independently from each other selected from the group    consisting of Me, ^(i)Pr, ^(t)Bu, CN, CF₃, and Ph,-   and N(Ph)₂.

In a further embodiment of the invention, R^(I), R^(III), R^(IV), andR^(V) is independently from another selected from the group consistingof:

-   hydrogen, deuterium, halogen, Me, ^(i)Pr, ^(t)Bu, CN, CF₃,-   Ph, which is optionally substituted with one or more substituents    independently from each other selected from the group consisting of    Me, ^(i)Pr, ^(t)Bu, CN, CF₃, and Ph,-   pyridinyl, which is optionally substituted with one or more    substituents independently from each other selected from the group    consisting of Me, ^(i)Pr, ^(t)Bu, CN, CF₃, and Ph,-   pyrimidinyl, which is optionally substituted with one or more    substituents independently from each other selected from the group    consisting of Me, ^(i)Pr, ^(t)Bu, CN, CF₃, and Ph, and-   triazinyl, which is optionally substituted with one or more    substituents independently from each other selected from the group    consisting of Me, ^(i)Pr, ^(t)Bu, CN, CF₃, and Ph;-   and R^(II) and R^(V) is independently from another selected from the    group consisting of: hydrogen, deuterium, Me, ^(i)Pr, ^(t)Bu,-   Ph, which is optionally substituted with one or more substituents    independently from each other selected from the group consisting of    Me, ^(i)Pr, ^(t)Bu, and Ph,-   carbazolyl, which is optionally substituted with one or more    substituents independently from each other selected from the group    consisting of Me, ^(i)Pr, ^(t)Bu, CN, CF₃, and Ph,-   and N(Ph)₂.

In a further embodiment of the invention, R^(I), R^(III), R^(IV), andR^(VI) is independently from another selected from the group consistingof hydrogen, deuterium, Me, ^(i)Pr, ^(t)Bu, CN, CF₃, and

Ph, which is optionally substituted with one or more substituentsindependently from each other selected from the group consisting of Me,^(i)Pr, ^(t)Bu, CN, CF₃, and Ph;

R^(II) and R^(V) is independently from another selected from the groupconsisting of hydrogen, deuterium, Me, ^(i)Pr, ^(t)Bu,

-   -   Ph, which is optionally substituted with one or more        substituents independently from each other selected from the        group consisting of Me, ^(i)Pr, ^(t)Bu, and Ph,    -   carbazolyl, which is optionally substituted with one or more        substituents independently from each other selected from the        group consisting of Me, ^(t)Bu, and Ph, and N(Ph)₂.

In a further embodiment of the invention, R², R⁴, R^(I), R^(III),R^(IV), and R^(VI) is independently from another selected from the groupconsisting of:

-   hydrogen, deuterium, halogen, Me, ^(i)Pr, ^(t)Bu, CN, CF₃,-   Ph, which is optionally substituted with one or more substituents    independently from each other selected from the group consisting of    Me, ^(i)Pr, ^(t)Bu, CN, CF₃, and Ph,-   pyridinyl, which is optionally substituted with one or more    substituents independently from each other selected from the group    consisting of Me, ^(i)Pr, ^(t)Bu, CN, CF₃, and Ph,-   pyrimidinyl, which is optionally substituted with one or more    substituents independently from each other selected from the group    consisting of Me, ^(i)Pr, ^(t)Bu, CN, CF₃, and Ph, and-   triazinyl, which is optionally substituted with one or more    substituents independently from each other selected from the group    consisting of Me, ^(i)Pr, ^(t)Bu, CN, CF₃, and Ph; and R³, R^(II)    and R^(V) is independently from another selected from the group    consisting of: hydrogen, deuterium, Me, ^(i)Pr, ^(t)Bu,-   Ph, which is optionally substituted with one or more substituents    independently from each other selected from the group consisting of    Me, ^(i)Pr, ^(t)Bu, and Ph,-   carbazolyl, which is optionally substituted with one or more    substituents independently from each other selected from the group    consisting of Me, ^(i)Pr, ^(t)Bu, CN, CF₃, and Ph,-   and N(Ph)₂.

In a further embodiment of the invention, R², R⁴, R^(I), R^(III),R^(IV), and R^(VI) is independently from another selected from the groupconsisting of hydrogen, deuterium, Me, ^(i)Pr, ^(t)Bu, CN, CF₃, and

Ph, which is optionally substituted with one or more substituentsindependently from each other selected from the group consisting of Me,^(i)Pr, ^(t)Bu, CN, CF₃, and Ph;

R³, R^(II) and R^(V) is independently from another selected from thegroup consisting of hydrogen, deuterium, Me, ^(i)Pr, ^(t)Bu,

-   Ph, which is optionally substituted with one or more substituents    independently from each other selected from the group consisting of    Me, ^(i)Pr, ^(t)Bu, and Ph,-   carbazolyl, which is optionally substituted with one or more    substituents independently from each other selected from the group    consisting of Me, ^(t)Bu, and Ph, and N(Ph)₂.

In a further embodiment of the invention, R², R⁴, R^(I), R^(III), R^(V),and R^(VI) are each H;

-   and R^(II), R^(V) and R³ is selected from the group consisting of    hydrogen, deuterium, Me, ^(i)Pr, ^(t)Bu, CN, CF₃,-   Ph, which is optionally substituted with one or more substituents    independently from each other selected from the group consisting of    Me, ^(i)Pr, ^(t)Bu, CN, CF₃, and Ph,-   carbazolyl, which is optionally substituted with one or more    substituents independently from each other selected from the group    consisting of Me, ^(t)Bu, and Ph,-   and N(Ph)₂.

In a further embodiment of the invention, R², R⁴, R^(I), R^(II),R^(III), R^(IV), R^(V), and R^(VI) are each H

And R³ is selected from the group consisting of hydrogen, deuterium, Me,^(i)Pr, ^(t)Bu, CN, CF₃,

-   Ph, which is optionally substituted with one or more substituents    independently from each other selected from the group consisting of    Me, ^(i)Pr, ^(t)Bu, CN, CF₃, and Ph,-   carbazolyl, which is optionally substituted with one or more    substituents independently from each other selected from the group    consisting of Me, ^(t)Bu, and Ph,-   and N(Ph)₂.

In a further embodiment of the invention, R^(I), R^(II), R^(III),R^(IV), R^(V), and, R^(VI) and R^(x) are each H.

In a further embodiment of the invention, R³, R² and R⁴ are each H.

In a further embodiment of the invention, R³, R², R⁴, R^(I), R^(II),R^(III), R^(IV), R^(V), and R^(VI) are each H.

In one embodiment of the invention, R¹ is C₆-C₃₀-aryl,

-   -   which is optionally substituted with one or more substituents        independently from each other selected from the group consisting        of Me, ^(i)Pr, ^(t)Bu, CN, CF₃, and Ph.

In a further embodiment of the invention, R¹ is phenyl or mesityl.

In a further embodiment of the invention, the organic molecules consistof a structure of one of Formulas II to XXI:

As used throughout the present application, the terms “aryl” and“aromatic” may be understood in the broadest sense as any mono-, bi- orpolycyclic aromatic moieties. Accordingly, an aryl group contains 6 to60 aromatic ring atoms, and a heteroaryl group contains 5 to 60 aromaticring atoms, of which at least one is a heteroatom. Notwithstanding,throughout the application the number of aromatic ring atoms may begiven as subscripted number in the definition of certain substituents.In particular, the heteroaromatic ring includes one to threeheteroatoms. Again, the terms “heteroaryl” and “heteroaromatic” may beunderstood in the broadest sense as any mono-, bi- or polycyclichetero-aromatic moieties that include at least one heteroatom. Theheteroatoms may at each occurrence be the same or different and beindividually selected from the group consisting of N, O and S.Accordingly, the term “arylene” refers to a divalent substituent thatbears two binding sites to other molecular structures and therebyserving as a linker structure. In case, a group in the exemplaryembodiments is defined differently from the definitions given here, forexample, the number of aromatic ring atoms or number of heteroatomsdiffers from the given definition, the definition in the exemplaryembodiments is to be applied. According to the invention, a condensed(annulated) aromatic or heteroaromatic polycycle is built of two or moresingle aromatic or heteroaromatic cycles, which formed the polycycle viaa condensation reaction.

In particular, as used throughout the present application, the term“aryl group or heteroaryl group” comprises groups which can be bound viaany position of the aromatic or heteroaromatic group, derived frombenzene, naphthaline, anthracene, phenanthrene, pyrene, dihydropyrene,chrysene, perylene, fluoranthene, benzanthracene, benzphenanthrene,tetracene, pentacene, benzpyrene, furan, benzofuran, isobenzofuran,dibenzofuran, thiophene, benzothiophene, isobenzothiophene,dibenzothiophene; pyrrole, indole, isoindole, carbazole, pyridine,quinoline, isoquinoline, acridine, phenanthridine, benzo-5,6-quinoline,benzo-6,7-quinoline, benzo-7,8-quinoline, phenothiazine, phenoxazine,pyrazole, indazole, imidazole, benzimidazole, naphthoimidazole,phenanthroimidazole, pyridoimidazole, pyrazinoimidazole,quinoxalinoimidazole, oxazole, benzoxazole, napthooxazole, anthroxazol,phenanthroxazol, isoxazole, 1,2-thiazole, 1,3-thiazole, benzothiazole,pyridazine, benzopyridazine, pyrimidine, benzopyrimidine,1,3,5-triazine, quinoxaline, pyrazine, phenazine, naphthyridine,carboline, benzocarboline, phenanthroline, 1,2,3-triazole,1,2,4-triazole, benzotriazole, 1,2,3-oxadiazole, 1,2,4-oxadiazole,1,2,5-oxadiazole, 1,2,3,4-tetrazine, purine, pteridine, indolizine andbenzothiadiazole or combinations of the abovementioned groups.

As used throughout the present application, the term “cyclic group” maybe understood in the broadest sense as any mono-, bi- or polycyclicmoieties.

As used throughout the present application, the term “biphenyl” as asubstituent may be understood in the broadest sense as ortho-biphenyl,meta-biphenyl, or para-biphenyl, wherein ortho, meta and para is definedin regard to the binding site to another chemical moiety.

As used throughout the present application, the term “alkyl group” maybe understood in the broadest sense as any linear, branched, or cyclicalkyl substituent. In particular, the term alkyl comprises thesubstituents methyl (Me), ethyl (Et), n-propyl (nPr), i-propyl (^(i)Pr),cyclopropyl, n-butyl (^(n)Bu), i-butyl (^(i)Bu), s-butyl (^(s)Bu),t-butyl (^(t)Bu), cyclobutyl, 2-methylbutyl, n-pentyl, s-pentyl,t-pentyl, 2-pentyl, neo-pentyl, cyclopentyl, n-hexyl, s-hexyl, t-hexyl,2-hexyl, 3-hexyl, neo-hexyl, cyclohexyl, 1-methylcyclopentyl,2-methylpentyl, n-heptyl, 2-heptyl, 3-heptyl, 4-heptyl, cycloheptyl,1-methylcyclohexyl, n-octyl, 2-ethylhexyl, cyclooctyl,1-bicyclo[2,2,2]octyl, 2-bicyclo[2,2,2]-octyl, 2-(2,6-dimethyl)octyl,3-(3,7-dimethyl)octyl, adamantyl, 2,2,2-trifluorethyl,1,1-dimethyl-n-hex-1-yl, 1,1-dimethyl-n-hept-1-yl,1,1-dimethyl-n-oct-1-yl, 1,1-dimethyl-n-dec-1-yl,1,1-dimethyl-n-dodec-1-yl, 1,1-dimethyl-n-tetradec-1-yl,1,1-dimethyl-n-hexadec-1-yl, 1,1-dimethyl-n-octadec-1-yl,1,1-diethyl-n-hex-1-yl, 1,1-diethyl-n-hept-1-yl, 1,1-diethyl-n-oct-1-yl,1,1-diethyl-n-dec-1-yl, 1,1-diethyl-n-dodec-1-yl,1,1-diethyl-n-tetradec-1-yl, 1,1-diethyln-n-hexadec-1-yl,1,1-diethyl-n-octadec-1-yl, 1-(n-propyl)-cyclohex-1-yl,1-(n-butyl)-cyclohex-1-yl, 1-(n-hexyl)-cyclohex-1-yl,1-(n-octyl)-cyclohex-1-yl and 1-(n-decyl)-cyclohex-1-yl.

As used throughout the present application, the term “alkenyl” compriseslinear, branched, and cyclic alkenyl substituents. The term alkenylgroup exemplarily comprises the substituents ethenyl, propenyl, butenyl,pentenyl, cyclopentenyl, hexenyl, cyclohexenyl, heptenyl, cycloheptenyl,octenyl, cyclooctenyl or cyclooctadienyl.

As used throughout the present application, the term “alkynyl” compriseslinear, branched, and cyclic alkynyl substituents. The term alkynylgroup exemplarily comprises ethynyl, propynyl, butynyl, pentynyl,hexynyl, heptynyl or octynyl.

As used throughout the present application, the term “alkoxy” compriseslinear, branched, and cyclic alkoxy substituents. The term alkoxy groupexemplarily comprises methoxy, ethoxy, n-propoxy, i-propoxy, n-butoxy,i-butoxy, s-butoxy, t-butoxy and 2-methylbutoxy.

As used throughout the present application, the term “thioalkoxy”comprises linear, branched, and cyclic thioalkoxy substituents, in whichthe O of the exemplarily alkoxy groups is replaced by S.

As used throughout the present application, the terms “halogen” and“halo” may be understood in the broadest sense as being preferablyfluorine, chlorine, bromine or iodine.

Whenever hydrogen (H) is mentioned herein, it could also be replaced bydeuterium at each occurrence.

It is understood that when a molecular fragment is described as being asubstituent or otherwise attached to another moiety, its name may bewritten as if it were a fragment (e.g. naphtyl, dibenzofuryl) or as ifit were the whole molecule (e.g. naphthalene, dibenzofuran).

As used herein, these different ways of designating a substituent orattached fragment are considered to be equivalent.

In one embodiment, the organic molecules according to the invention havean excited state lifetime of not more than 150 μs, of not more than 100μs, in particular of not more than 50 μs, more preferably of not morethan 10 μs or not more than 7 μs in a film of poly(methyl methacrylate)(PMMA) with 10% by weight of organic molecule at room temperature.

In a further embodiment of the invention, the organic moleculesaccording to the invention have an emission peak in the visible ornearest ultraviolet range, i.e., in the range of a wavelength of from380 to 800 nm, with a full width at half maximum of less than 0.40 eV,preferably less than 0.35 eV, more preferably less than 0.33 eV, evenmore preferably less than 0.30 eV or even less than 0.28 eV in a film ofpoly(methyl methacrylate) (PMMA) with 10% by weight of organic moleculeat room temperature.

Orbital and excited state energies can be determined either by means ofexperimental methods or by calculations employing quantum-chemicalmethods, in particular density functional theory calculations. Theenergy of the highest occupied molecular orbital E^(HOMO) is determinedby methods known to the person skilled in the art from cyclicvoltammetry measurements with an accuracy of 0.1 eV. The energy of thelowest unoccupied molecular orbital E^(LUMO) is calculated asE^(HOMO)+E^(gap), wherein E^(gap) is determined as follows: For hostcompounds, the onset of the emission spectrum of a film with 10% byweight of host in poly(methyl methacrylate) (PMMA) is used as E^(gap),unless stated otherwise. For emitter molecules, E^(gap) is determined asthe energy at which the excitation and emission spectra of a film with10% by weight of emitter in PMMA cross.

The energy of the first excited triplet state T1 is determined from theonset of the emission spectrum at low temperature, typically at 77 K.For host compounds, where the first excited singlet state and the lowesttriplet state are energetically separated by >0.4 eV, thephosphorescence is usually visible in a steady-state spectrum in2-Me-THF. The triplet energy can thus be determined as the onset of thephosphorescence spectrum. For TADF emitter molecules, the energy of thefirst excited triplet state T1 is determined from the onset of thedelayed emission spectrum at 77 K, if not otherwise stated, measured ina film of PMMA with 10% by weight of emitter. Both for host and emittercompounds, the energy of the first excited singlet state S1 isdetermined from the onset of the emission spectrum, if not otherwisestated, measured in a film of PMMA with 10% by weight of host or emittercompound.

The onset of an emission spectrum is determined by computing theintersection of the tangent to the emission spectrum with the x-axis.The tangent to the emission spectrum is set at the high-energy side ofthe emission band and at the point at half maximum of the maximumintensity of the emission spectrum.

A further aspect of the invention relates to a process for preparing theorganic molecule of the invention (with an optional subsequentreaction), wherein butyllithium (BuLi) and boron tribromide (BBr₃) areused as reactants:

A further aspect of the invention relates to the use of an organicmolecule of the invention as a luminescent emitter or as an absorber,and/or as a host material and/or as an electron transport material,and/or as a hole injection material, and/or as a hole blocking materialin an optoelectronic device.

A preferred embodiment relates to the use of an organic moleculeaccording to the invention as a luminescent emitter in an optoelectronicdevice.

The optoelectronic device may be understood in the broadest sense as anydevice based on organic materials that is suitable for emitting light inthe visible or nearest ultraviolet (UV) range, i.e., in the range of awavelength of from 380 to 800 nm. More preferably, the optoelectronicdevice may be able to emit light in the visible range, i.e., of from 400nm to 800 nm.

In the context of such use, the optoelectronic device is moreparticularly selected from the group consisting of:

-   -   organic light-emitting diodes (OLEDs),    -   light-emitting electrochemical cells,    -   OLED sensors, especially in gas and vapor sensors that are not        hermetically shielded to the surroundings,    -   organic diodes,    -   organic solar cells,    -   organic transistors,    -   organic field-effect transistors,    -   organic lasers and    -   down-conversion elements.

In a preferred embodiment in the context of such use, the optoelectronicdevice is a device selected from the group consisting of an organiclight emitting diode (OLED), a light emitting electrochemical cell(LEC), and a light-emitting transistor.

In the case of the use, the fraction of the organic molecule accordingto the invention in the emission layer in an optoelectronic device, moreparticularly in an OLED, is 1% to 99% by weight, more particularly 3% to80% by weight. In an alternative embodiment, the proportion of theorganic molecule in the emission layer is 100% by weight.

In one embodiment, the light-emitting layer comprises not only theorganic molecules according to the invention, but also a host materialwhose triplet (T1) and singlet (Si) energy levels are energeticallyhigher than the triplet (T1) and singlet (Si) energy levels of theorganic molecule.

A further aspect of the invention relates to a composition comprising orconsisting of:

-   (a) at least one organic molecule according to the invention, in    particular in the form of an emitter and/or a host, and-   (b) one or more emitter and/or host materials, which differ from the    organic molecule according to the invention and-   (c) optional one or more dyes and/or one or more solvents.

In one embodiment, the light-emitting layer comprises (or essentiallyconsists of) a composition comprising or consisting of:

-   (a) at least one organic molecule according to the invention, in    particular in the form of an emitter and/or a host, and-   (b) one or more emitter and/or host materials, which differ from the    organic molecule according to the invention and-   (c) optional one or more dyes and/or one or more solvents.

In a particular embodiment, the light-emitting layer EML comprises (oressentially consists of) a composition comprising or consisting of:

-   (i) 1-50% by weight, preferably 5-40% by weight, in particular    10-30% by weight, of one or more organic molecules according to the    invention;-   (ii) 5-99% by weight, preferably 30-94.9% by weight, in particular    40-89% by weight, of at least one host compound H; and-   (iii) optionally 0-94% by weight, preferably 0.1-65% by weight, in    particular 1-50% by weight, of at least one further host compound D    with a structure differing from the structure of the molecules    according to the invention; and-   (iv) optionally 0-94% by weight, preferably 0-65% by weight, in    particular 0-50% by weight, of a solvent; and-   (v) optionally 0-30% by weight, in particular 0-20% by weight,    preferably 0-5% by weight, of at least one further emitter molecule    F with a structure differing from the structure of the molecules    according to the invention.

Preferably, energy can be transferred from the host compound H to theone or more organic molecules according to the invention, in particulartransferred from the first excited triplet state T1(H) of the hostcompound H to the first excited triplet state T1(E) of the one or moreorganic molecules according to the invention E and/or from the firstexcited singlet state S1(H) of the host compound H to the first excitedsinglet state S1(E) of the one or more organic molecules according tothe invention E.

In a further embodiment, the light-emitting layer EML comprises (oressentially consists of) a composition comprising or consisting of:

-   (i) 1-50% by weight, preferably 5-40% by weight, in particular    10-30% by weight, of one organic molecule according to the    invention;-   (ii) 5-99% by weight, preferably 30-94.9% by weight, in particular    40-89% by weight, of one host compound H; and-   (iii) optionally 0-94% by weight, preferably 0.1-65% by weight, in    particular 1-50% by weight, of at least one further host compound D    with a structure differing from the structure of the molecules    according to the invention; and-   (iv) optionally 0-94% by weight, preferably 0-65% by weight, in    particular 0-50% by weight, of a solvent; and-   (v) optionally 0-30% by weight, in particular 0-20% by weight,    preferably 0-5% by weight, of at least one further emitter molecule    F with a structure differing from the structure of the molecules    according to the invention.

In one embodiment, the host compound H has a highest occupied molecularorbital HOMO(H) having an energy E^(HOMO)(H) in the range of from −5 to−6.5 eV and the at least one further host compound D has a highestoccupied molecular orbital HOMO(D) having an energy E^(HOMO)(D), whereinE^(HOMO)(H)>E^(HOMO)(D).

In a further embodiment, the host compound H has a lowest unoccupiedmolecular orbital LUMO(H) having an energy E^(LUMO)(H) and the at leastone further host compound D has a lowest unoccupied molecular orbitalLUMO(D) having an energy E^(LUMO)(D), wherein E^(LUMO)(H)>E^(LUMO)(D).

In one embodiment, the host compound H has a highest occupied molecularorbital HOMO(H) having an energy E^(HOMO)(H) and a lowest unoccupiedmolecular orbital LUMO(H) having an energy E^(LUMO)(H), and

-   -   the at least one further host compound D has a highest occupied        molecular orbital HOMO(D) having an energy E^(HOMO)(D) and a        lowest unoccupied molecular orbital LUMO(D) having an energy        E^(LUMO)(D),    -   the organic molecule according to the invention E has a highest        occupied molecular orbital HOMO(E) having an energy E^(HOMO)(E)        and a lowest unoccupied molecular orbital LUMO(E) having an        energy E^(LUMO)(E),        wherein        E^(HOMO)(H)>E^(HOMO)(D) and the difference between the energy        level of the highest occupied molecular orbital HOMO(E) of the        organic molecule according to the invention E (E^(HOMO)(E)) and        the energy level of the highest occupied molecular orbital        HOMO(H) of the host compound H (E^(HOMO)(H)) is between −0.5 eV        and 0.5 eV, more preferably between −0.3 eV and 0.3 eV, even        more preferably between −0.2 eV and 0.2 eV or even between −0.1        eV and 0.1 eV; and        E^(LUMO)(H)>E^(LUMO)(D) and the difference between the energy        level of the lowest unoccupied molecular orbital LUMO(E) of the        organic molecule according to the invention E (E^(LUMO)(E)) and        the lowest unoccupied molecular orbital LUMO(D) of the at least        one further host compound D (E^(LUMO)(D)) is between −0.5 eV and        0.5 eV, more preferably between −0.3 eV and 0.3 eV, even more        preferably between −0.2 eV and 0.2 eV or even between −0.1 eV        and 0.1 eV.

In one embodiment of the invention the host compound D and/or the hostcompound H is a thermally-activated delayed fluorescence(TADF)-material. TADF materials exhibit a ΔE_(ST) value, whichcorresponds to the energy difference between the first excited singletstate (S1) and the first excited triplet state (T1), of less than 2500cm⁻¹. Preferably the TADF material exhibits a ΔE_(ST) value of less than3000 cm⁻¹, more preferably less than 1500 cm⁻¹, even more preferablyless than 1000 cm⁻¹ or even less than 500 cm⁻¹.

In one embodiment, the host compound D is a TADF material and the hostcompound H exhibits a ΔE_(ST) Value of more than 2500 cm⁻¹. In aparticular embodiment, the host compound D is a TADF material and thehost compound H is selected from group consisting of CBP, mCP, mCBP,9-[3-(dibenzofuran-2-yl)phenyl]-9H-carbazole,9-[3-(dibenzofuran-2-yl)phenyl]-9H-carbazole,9-[3-(dibenzothiophen-2-yl)phenyl]-9H-carbazole,9-[3,5-bis(2-dibenzofuranyl)phenyl]-9H-carbazole and9-[3,5-bis(2-dibenzothiophenyl)phenyl]-9H-carbazole.

In one embodiment, the host compound H is a TADF material and the hostcompound D exhibits a ΔE_(ST) Value of more than 2500 cm⁻¹. In aparticular embodiment, the host compound H is a TADF material and thehost compound D is selected from group consisting of T2T(2,4,6-tris(biphenyl-3-yl)-1,3,5-triazine), T3T(2,4,6-tris(triphenyl-3-yl)-1,3,5-triazine) and/or TST(2,4,6-tris(9,9′-spirobifluorene-2-yl)-1,3,5-triazine).

In a further aspect, the invention relates to an optoelectronic devicecomprising an organic molecule or a composition of the type describedhere, more particularly in the form of a device selected from the groupconsisting of organic light-emitting diode (OLED), light-emittingelectrochemical cell, OLED sensor, more particularly gas and vapoursensors not hermetically externally shielded, organic diode, organicsolar cell, organic transistor, organic field-effect transistor, organiclaser and down-conversion element.

In a preferred embodiment, the optoelectronic device is a deviceselected from the group consisting of an organic light emitting diode(OLED), a light emitting electrochemical cell (LEC), and alight-emitting transistor.

In one embodiment of the optoelectronic device of the invention, theorganic molecule according to the invention E is used as emissionmaterial in a light-emitting layer EML.

In one embodiment of the optoelectronic device of the invention, thelight-emitting layer EML consists of the composition according to theinvention described here.

When the optoelectronic device is an OLED, it may, for example, have thefollowing layer structure:

1. substrate

2. anode layer A

3. hole injection layer, HIL

4. hole transport layer, HTL

5. electron blocking layer, EBL

6. emitting layer, EML

7. hole blocking layer, HBL

8. electron transport layer, ETL

9. electron injection layer, EIL

10. cathode layer,

wherein the OLED comprises each layer selected from the group of HIL,HTL, EBL, HBL, ETL, and EIL only optionally, different layers may bemerged and the OLED may comprise more than one layer of each layer typedefined above.

Furthermore, the optoelectronic device may, in certain embodiments,comprise one or more protective layers protecting the device fromdamaging exposure to harmful species in the environment including, forexample, moisture, vapor and/or gases.

In one embodiment of the invention, the optoelectronic device is anOLED, with the following inverted layer structure:

1. substrate

2. cathode layer

3. electron injection layer, EIL

4. electron transport layer, ETL

5. hole blocking layer, HBL

6. emitting layer, B

7. electron blocking layer, EBL

8. hole transport layer, HTL

9. hole injection layer, HIL

10. anode layer A

wherein the OLED comprises each layer selected from the group of HIL,HTL, EBL, HBL, ETL, and EIL only optionally, different layers may bemerged and the OLED may comprise more than one layer of each layer typesdefined above.

In one embodiment of the invention, the optoelectronic device is anOLED, which may have a stacked architecture. In this architecture,contrary to the typical arrangement in which the OLEDs are placed sideby side, the individual units are stacked on top of each other. Blendedlight may be generated with OLEDs exhibiting a stacked architecture, inparticular white light may be generated by stacking blue, green and redOLEDs. Furthermore, the OLED exhibiting a stacked architecture maycomprise a charge generation layer (CGL), which is typically locatedbetween two OLED subunits and typically consists of a n-doped andp-doped layer with the n-doped layer of one CGL being typically locatedcloser to the anode layer.

In one embodiment of the invention, the optoelectronic device is anOLED, which comprises two or more emission layers between anode andcathode. In particular, this so-called tandem OLED comprises threeemission layers, wherein one emission layer emits red light, oneemission layer emits green light and one emission layer emits bluelight, and optionally may comprise further layers such as chargegeneration layers, blocking or transporting layers between theindividual emission layers. In a further embodiment, the emission layersare adjacently stacked. In a further embodiment, the tandem OLEDcomprises a charge generation layer between each two emission layers. Inaddition, adjacent emission layers or emission layers separated by acharge generation layer may be merged.

The substrate may be formed by any material or composition of materials.Most frequently, glass slides are used as substrates. Alternatively,thin metal layers (e.g., copper, gold, silver or aluminum films) orplastic films or slides may be used. This may allow for a higher degreeof flexibility. The anode layer A is mostly composed of materialsallowing to obtain an (essentially) transparent film. As at least one ofboth electrodes should be (essentially) transparent in order to allowlight emission from the OLED, either the anode layer A or the cathodelayer C is transparent. Preferably, the anode layer A comprises a largecontent or even consists of transparent conductive oxides (TCOs). Suchanode layer A may, for example, comprise indium tin oxide, aluminum zincoxide, fluorine doped tin oxide, indium zinc oxide, PbO, SnO, zirconiumoxide, molybdenum oxide, vanadium oxide, tungsten oxide, graphite, dopedSi, doped Ge, doped GaAs, doped polyaniline, doped polypyrrol and/ordoped polythiophene.

The anode layer A (essentially) may consist of indium tin oxide (ITO)(e.g., (InO₃)_(0.9)(SnO₂)_(0.1)).

The roughness of the anode layer A caused by the transparent conductiveoxides (TCOs) may be compensated by using a hole injection layer (HIL).Further, the HIL may facilitate the injection of quasi charge carriers(i.e., holes) in that the transport of the quasi charge carriers fromthe TCO to the hole transport layer (HTL) is facilitated. The holeinjection layer (HIL) may comprise poly-3,4-ethylendioxy thiophene(PEDOT), polystyrene sulfonate (PSS), MoO₂, V₂O₅, CuPC or CuI, inparticular a mixture of PEDOT and PSS. The hole injection layer (HIL)may also prevent the diffusion of metals from the anode layer A into thehole transport layer (HTL). The HIL may exemplarily comprise PEDOT:PSS(poly-3,4-ethylendioxy thiophene:polystyrene sulfonate), PEDOT(poly-3,4-ethylendioxy thiophene), mMTDATA(4,4′,4″-tris[phenyl(m-tolyl)amino]triphenylamine), Spiro-TAD(2,2′,7,7′-tetrakis(n,n-diphenylamino)-9,9′-spirobifluorene), DNTPD(N1,N1′-(biphenyl-4,4′-diyl)bis(N1-phenyl-N4,N4-di-m-tolylbenzene-1,4-diamine),NPB(N,N′-nis-(1-naphthalenyl)-N,N′-bis-phenyl-(1,1′-biphenyl)-4,4′-diamine),NPNPB (N,N′-diphenyl-N,N′-di-[4-(N,N-diphenyl-amino)phenyl]benzidine),MeO-TPD (N,N,N′,N′-tetrakis(4-methoxyphenyl)benzidine), HAT-CN(1,4,5,8,9,11-hexaazatriphenylen-hexacarbonitrile) and/or Spiro-NPD(N,N′-diphenyl-N, N′-bis-(1-naphthyl)-9,9′-spirobifluorene-2,7-diamine).

Adjacent to the anode layer A or hole injection layer (HIL), a holetransport layer (HTL) is typically located. Herein, any hole transportcompound may be used. For example, electron-rich heteroaromaticcompounds such as triarylamines and/or carbazoles may be used as holetransport compound. The HTL may decrease the energy barrier between theanode layer A and the light-emitting layer EML. The hole transport layer(HTL) may also be an electron blocking layer (EBL). Preferably, holetransport compounds bear comparably high energy levels of their tripletstates T1. For example, the hole transport layer (HTL) may comprise astar-shaped heterocycle such as tris(4-carbazoyl-9-ylphenyl)amine(TCTA), poly-TPD (poly(4-butylphenyl-diphenyl-amine)), [alpha]-NPD(poly(4-butylphenyl-diphenyl-amine)), TAPC(4,4′-cyclohexyliden-bis[N,N-bis(4-methylphenyl)benzenamine]), 2-TNATA(4,4′,4″-tris[2-naphthyl(phenyl)amino]triphenylamine), Spiro-TAD, DNTPD,NPB, NPNPB, MeO-TPD, HAT-CN and/or TrisPcz(9,9′-diphenyl-6-(9-phenyl-9H-carbazol-3-yl)-9H,9′H-3,3′-bicarbazole).In addition, the HTL may comprise a p-doped layer, which may be composedof an inorganic or organic dopant in an organic hole-transportingmatrix. Transition metal oxides such as vanadium oxide, molybdenum oxideor tungsten oxide may exemplarily be used as inorganic dopant.Tetrafluorotetracyanoquinodimethane (F₄-TCNQ),copper-pentafluorobenzoate (Cu(I)pFBz) or transition metal complexes mayexemplarily be used as organic dopant.

The EBL may exemplarily comprise mCP (1,3-bis(carbazol-9-yl)benzene),TCTA, 2-TNATA, mCBP (3,3-di(9H-carbazol-9-yl)biphenyl), tris-Pcz, CzSi(9-(4-tert-Butylphenyl)-3,6-bis(triphenylsilyl)-9H-carbazole), and/orDCB (N,N′-dicarbazolyl-1,4-dimethylbenzene).

Adjacent to the hole transport layer (HTL), the light-emitting layer EMLis typically located. The light-emitting layer EML comprises at leastone light emitting molecule. Particularly, the EML comprises at leastone light emitting molecule according to the invention E. In oneembodiment, the light-emitting layer comprises only the organicmolecules according to the invention. Typically, the EML additionallycomprises one or more host materials H. Exemplarily, the host material His selected from CBP (4,4′-Bis-(N-carbazolyl)-biphenyl), mCP, mCBP Sif87(dibenzo[b,d]thiophen-2-yltriphenylsilane), CzSi, Sif88(dibenzo[b,d]thiophen-2-yl)diphenylsilane), DPEPO(bis[2-(diphenylphosphino)phenyl] ether oxide),9-[3-(dibenzofuran-2-yl)phenyl]-9H-carbazole,9-[3-(dibenzofuran-2-yl)phenyl]-9H-carbazole,9-[3-(dibenzothiophen-2-yl)phenyl]-9H-carbazole,9-[3,5-bis(2-dibenzofuranyl)phenyl]-9H-carbazole,9-[3,5-bis(2-dibenzothiophenyl)phenyl]-9H-carbazole, T2T(2,4,6-tris(biphenyl-3-yl)-1,3,5-triazine), T3T(2,4,6-tris(triphenyl-3-yl)-1,3,5-triazine) and/or TST(2,4,6-tris(9,9′-spirobifluorene-2-yl)-1,3,5-triazine). The hostmaterial H typically should be selected to exhibit first triplet (T1)and first singlet (S1) energy levels, which are energetically higherthan the first triplet (T1) and first singlet (S1) energy levels of theorganic molecule.

In one embodiment of the invention, the EML comprises a so-calledmixed-host system with at least one hole-dominant host and oneelectron-dominant host. In a particular embodiment, the EML comprisesexactly one light emitting organic molecule according to the inventionand a mixed-host system comprising T2T as electron-dominant host and ahost selected from CBP, mCP, mCBP,9-[3-(dibenzofuran-2-yl)phenyl]-9H-carbazole,9-[3-(dibenzofuran-2-yl)phenyl]-9H-carbazole,9-[3-(dibenzothiophen-2-yl)phenyl]-9H-carbazole,9-[3,5-bis(2-dibenzofuranyl)phenyl]-9H-carbazole and9-[3,5-bis(2-dibenzothiophenyl)phenyl]-9H-carbazole as hole-dominanthost. In a further embodiment the EML comprises 50-80% by weight,preferably 60-75% by weight of a host selected from CBP, mCP, mCBP,9-[3-(dibenzofuran-2-yl)phenyl]-9H-carbazole,9-[3-(dibenzofuran-2-yl)phenyl]-9H-carbazole,9-[3-(dibenzothiophen-2-yl)phenyl]-9H-carbazole,9-[3,5-bis(2-dibenzofuranyl)phenyl]-9H-carbazole and9-[3,5-bis(2-dibenzothiophenyl)phenyl]-9H-carbazole; 10-45% by weight,preferably 15-30% by weight of T2T and 5-40% by weight, preferably10-30% by weight of light emitting molecule according to the invention.

Adjacent to the light-emitting layer EML, an electron transport layer(ETL) may be located. Herein, any electron transporter may be used.Exemplarily, electron-poor compounds such as, e.g., benzimidazoles,pyridines, triazoles, oxadiazoles (e.g., 1,3,4-oxadiazole),phosphinoxides and sulfone, may be used. An electron transporter mayalso be a star-shaped heterocycle such as1,3,5-tri(1-phenyl-1H-benzo[d]imidazol-2-yl)phenyl (TPBi). The ETL maycomprise NBphen(2,9-bis(naphthalen-2-yl)-4,7-diphenyl-1,10-phenanthroline), Alq₃(Aluminum-tris(8-hydroxyquinoline)), TSPO1(diphenyl-4-triphenylsilylphenyl-phosphinoxide), BPyTP2(2,7-di(2,2′-bipyridin-5-yl)triphenyle), Sif87(dibenzo[b,d]thiophen-2-yltriphenylsilane), Sif88(dibenzo[b,d]thiophen-2-yl)diphenylsilane), BmPyPhB(1,3-bis[3,5-di(pyridin-3-yl)phenyl]benzene) and/or BTB(4,4′-bis-[2-(4,6-diphenyl-1,3,5-triazinyl)]-1,1′-biphenyl). Optionally,the ETL may be doped with materials such as Liq. The electron transportlayer (ETL) may also block holes or a holeblocking layer (HBL) isintroduced.

The HBL may, for example, comprise BCP(2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline=Bathocuproine), BAlq(bis(8-hydroxy-2-methylquinoline)-(4-phenylphenoxy)aluminum), NBphen(2,9-bis(naphthalen-2-yl)-4,7-diphenyl-1,10-phenanthroline), Alq₃(Aluminum-tris(8-hydroxyquinoline)), TSPO1(diphenyl-4-triphenylsilylphenyl-phosphinoxide), T2T(2,4,6-tris(biphenyl-3-yl)-1,3,5-triazine), T3T(2,4,6-tris(triphenyl-3-yl)-1,3,5-triazine), TST(2,4,6-tris(9,9′-spirobifluorene-2-yl)-1,3,5-triazine), and/or TCB/TCP(1,3,5-tris(N-carbazolyl)benzol/1,3,5-tris(carbazol)-9-yl) benzene).

Adjacent to the electron transport layer (ETL), a cathode layer C may belocated. The cathode layer C may, for example, comprise or may consistof a metal (e.g., Al, Au, Ag, Pt, Cu, Zn, Ni, Fe, Pb, LiF, Ca, Ba, Mg,In, W, or Pd) or a metal alloy. For practical reasons, the cathode layermay also consist of (essentially) intransparent metals such as Mg, Ca orAl. Alternatively or additionally, the cathode layer C may also comprisegraphite and or carbon nanotubes (CNTs). Alternatively, the cathodelayer C may also consist of nanoscalic silver wires.

An OLED may further, optionally, comprise a protection layer between theelectron transport layer (ETL) and the cathode layer C (which may bedesignated as electron injection layer (EIL)). This layer may compriselithium fluoride, cesium fluoride, silver, Liq(8-hydroxyquinolinolatolithium), Li₂O, BaF₂, MgO and/or NaF.

Optionally, the electron transport layer (ETL) and/or a hole blockinglayer (HBL) may also comprise one or more host compounds H.

In order to modify the emission spectrum and/or the absorption spectrumof the light-emitting layer EML further, the light-emitting layer EMLmay further comprise one or more further emitter molecules F. Such anemitter molecule F may be any emitter molecule known in the art.Preferably such an emitter molecule F is a molecule with a structurediffering from the structure of the molecules according to the inventionE. The emitter molecule F may optionally be a TADF emitter.Alternatively, the emitter molecule F may optionally be a fluorescentand/or phosphorescent emitter molecule which is able to shift theemission spectrum and/or the absorption spectrum of the light-emittinglayer EML. Exemplarily, the triplet and/or singlet excitons may betransferred from the organic emitter molecule according to the inventionto the emitter molecule F before relaxing to the ground state S0 byemitting light typically red-shifted in comparison to the light emittedby an organic molecule. Optionally, the emitter molecule F may alsoprovoke two-photon effects (i.e., the absorption of two photons of halfthe energy of the absorption maximum).

Optionally, an optoelectronic device (e.g., an OLED) may, for example,be an essentially white optoelectronic device. Exemplarily, such whiteoptoelectronic device may comprise at least one (deep) blue emittermolecule and one or more emitter molecules emitting green and/or redlight. Then, there may also optionally be energy transmittance betweentwo or more molecules as described above.

As used herein, if not defined more specifically in the particularcontext, the designation of the colors of emitted and/or absorbed lightis as follows:

violet: wavelength range of >380-420 nm;

deep blue: wavelength range of >420-480 nm;

sky blue: wavelength range of >480-500 nm;

green: wavelength range of >500-560 nm;

yellow: wavelength range of >560-580 nm;

orange: wavelength range of >580-620 nm;

red: wavelength range of >620-800 nm.

With respect to emitter molecules, such colors refer to the emissionmaximum. Therefore, exemplarily, a deep blue emitter has an emissionmaximum in the range of from >420 to 480 nm, a sky blue emitter has anemission maximum in the range of from >480 to 500 nm, a green emitterhas an emission maximum in a range of from >500 to 560 nm, a red emitterhas an emission maximum in a range of from >620 to 800 nm.

A deep blue emitter may preferably have an emission maximum of below 480nm, more preferably below 470 nm, even more preferably below 465 nm oreven below 460 nm. It will typically be above 420 nm, preferably above430 nm, more preferably above 440 nm or even above 450 nm.

Accordingly, a further aspect of the present invention relates to anOLED, which exhibits an external quantum efficiency at 1000 cd/m² ofmore than 8%, more preferably of more than 10%, more preferably of morethan 13%, even more preferably of more than 15% or even more than 20%and/or exhibits an emission maximum between 420 nm and 500 nm,preferably between 430 nm and 490 nm, more preferably between 440 nm and480 nm, even more preferably between 450 nm and 470 nm and/or exhibits aLT80 value at 500 cd/m² of more than 100 h, preferably more than 200 h,more preferably more than 400 h, even more preferably more than 750 h oreven more than 1000 h. Accordingly, a further aspect of the presentinvention relates to an OLED, whose emission exhibits a CIEy colorcoordinate of less than 0.45, preferably less than 0.30, more preferablyless than 0.20 or even more preferably less than 0.15 or even less than0.10.

A further aspect of the present invention relates to an OLED, whichemits light at a distinct color point. According to the presentinvention, the OLED emits light with a narrow emission band (small fullwidth at half maximum (FWHM)). In one aspect, the OLED according to theinvention emits light with a FWHM of the main emission peak of less than0.40 eV, preferably less than 0.35 eV, more preferably less than 0.33eV, even more preferably less than 0.30 eV or even less than 0.28 eV.

A further aspect of the present invention relates to an OLED, whichemits light with CIEx and CIEy color coordinates close to the CIEx(=0.131) and CIEy (=0.046) color coordinates of the primary color blue(CIEx=0.131 and CIEy=0.046) as defined by ITU-R Recommendation BT.2020(Rec. 2020) and thus is suited for the use in Ultra High Definition(UHD) displays, e.g. UHD-TVs. Accordingly, a further aspect of thepresent invention relates to an OLED, whose emission exhibits a CIExcolor coordinate of between 0.02 and 0.30, preferably between 0.03 and0.25, more preferably between 0.05 and 0.20 or even more preferablybetween 0.08 and 0.18 or even between 0.10 and 0.15 and/or a CIEy colorcoordinate of between 0.00 and 0.45, preferably between 0.01 and 0.30,more preferably between 0.02 and 0.20 or even more preferably between0.03 and 0.15 or even between 0.04 and 0.10.

In a further aspect, the invention relates to a method for producing anoptoelectronic component. In this case an organic molecule of theinvention is used.

The optoelectronic device, in particular the OLED according to thepresent invention can be fabricated by any means of vapor depositionand/or liquid processing. Accordingly, at least one layer is

-   -   prepared by means of a sublimation process,    -   prepared by means of an organic vapor phase deposition process,    -   prepared by means of a carrier gas sublimation process,    -   solution processed or printed.

The methods used to fabricate the optoelectronic device, in particularthe OLED according to the present invention are known in the art. Thedifferent layers are individually and successively deposited on asuitable substrate by means of subsequent deposition processes. Theindividual layers may be deposited using the same or differingdeposition methods.

Vapor deposition processes, for example, comprise thermal(co)evaporation, chemical vapor deposition and physical vapordeposition. For active matrix OLED display, an AMOLED backplane is usedas substrate. The individual layer may be processed from solutions ordispersions employing adequate solvents. Solution deposition processexemplarily comprise spin coating, dip coating and jet printing. Liquidprocessing may optionally be carried out in an inert atmosphere (e.g.,in a nitrogen atmosphere) and the solvent may optionally be completelyor partially removed by means known in the state of the art.

EXAMPLES

General Procedure for Synthesis:

Synthesis of Z1:

E1 (1.1 equivalents), E2 (1.1 equivalents), E3 (1.0 equivalent), K₂CO₃(4.0 equivalents) and copper powder (6.0 equivalents) were mixed in dryo-dichlorobenzene (ODCB) and stirred at 180° C. for 110 h. The insolublematerials were filtered off and washed with CH₂Cl₂. The combinedfiltrate was washed with water and extracted with CH₂Cl₂. The organicphase was dried over MgSO₄, filtered off, and concentrated under reducedpressure. The obtained crude product was washed with hexane to give Z1.

Synthesis of Z2:

To a microwave tube was added Z1 (1.0 equivalent) and1-n-butyl-3-methylimidazolium bromide ([bmim][Br]; 3.0 equivalents). Thereaction tube was flushed with argon and then was irradiated at 20 W forthe 10 min with air-flow cooling to prevent overheating. After cooled toroom temperature, the reaction mixture was acidified with 1 M HClsolution and extracted with ethyl acetate. The combined organic layerwas washed with water and brine, and dried over anhydrous MgSO₄ and thesolvent was evaporated under vacuum. Crude product was purified onsilica gel to afford Z2.

Synthesis of Z3:

Z2 (1.0 equivalent) was dissolved in DMF. K₂CO₃ (3.0 equivalents) wasadded and the mixture was stirred at 100° C. for 19 h. After addition of1 mol/L HCl, the products were extracted with CH₂Cl₂. The organic phasewas dried over Na₂SO₄, filtered off, and concentrated under reducedpressure. The obtained crude product was purified by silica gel shortcolumn chromatography (CH₂Cl₂) to give Z3.

Synthesis of P1:

Z3 (1.00 equivalents) was dissolved in diethyl ether and the solutionwas cooled to −78° C. tert-Butyllithium (^(t)BuLi) (4.00 equivalents)was added dropwise and the reaction mixture was allowed to warm up to 0°C. After stirring for 30 minutes at 0° C., the reaction mixture wascooled again to −78° C.

A solution of boronate ester compound [R¹B(OMe)₂ (1.2 equivalents)] indiethyl ether was added dropwise, the bath was removed and the reactionmixture was allowed to warm to room temperature (rt). Subsequently, thereaction mixture was heated at reflux overnight. Volatiles were removedunder reduced pressure and the crude purified by column chromatographyto afford the compound P1 as a solid product.

Cyclic Voltammetry

Cyclic voltammograms are measured from solutions having concentration of10⁻³ mol/L of the organic molecules in dichloromethane or a suitablesolvent and a suitable supporting electrolyte (e.g. 0.1 mol/L oftetrabutylammonium hexafluorophosphate). The measurements are conductedat room temperature under nitrogen atmosphere with a three-electrodeassembly (Working and counter electrodes: Pt wire, reference electrode:Pt wire) and calibrated using FeCp₂/FeCp₂ ⁺ as internal standard. TheHOMO data was corrected using ferrocene as internal standard againstSCE.

Density Functional Theory Calculation

Molecular structures are optimized employing the BP86 functional and theresolution of identity approach (RI). Excitation energies are calculatedusing the (BP86) optimized structures employing Time-Dependent DFT(TD-DFT) methods. Orbital and excited state energies are calculated withthe B3LYP functional. Def2-SVP basis sets (and a m4-grid for numericalintegration are used. The Turbomole program package is used for allcalculations.

Photophysical Measurements

Sample pretreatment: Spin-coating

Apparatus: Spin150, SPS euro.

The sample concentration is 10 mg/ml, dissolved in a suitable solvent.

Program: 1) 3 s at 400 U/min; 20 s at 1000 U/min at 1000 Upm/s. 3) 10 sat 4000 U/min at 1000 Upm/s. After coating, the films are tried at 70°C. for 1 min.

Photoluminescence Spectroscopy and TCSPC (Time-Correlated Single-PhotonCounting)

Steady-state emission spectroscopy is measured by a Horiba Scientific,Modell FluoroMax-4 equipped with a 150 W Xenon-Arc lamp, excitation- andemissions monochromators and a Hamamatsu R928 photomultiplier and atime-correlated single-photon counting option. Emissions and excitationspectra are corrected using standard correction fits.

Excited state lifetimes are determined employing the same system usingthe TCSPC method with FM-2013 equipment and a Horiba Yvon TCSPC hub.

Excitation Sources:

NanoLED 370 (wavelength: 371 nm, puls duration: 1.1 ns)

NanoLED 290 (wavelength: 294 nm, puls duration: <1 ns)

SpectraLED 310 (wavelength: 314 nm)

SpectraLED 355 (wavelength: 355 nm).

Data analysis (exponential fit) is done using the software suiteDataStation and DAS6 analysis software. The fit is specified using thechi-squared-test.

Photoluminescence Quantum Yield Measurements

For photoluminescence quantum yield (PLQY) measurements an Absolute PLQuantum Yield Measurement C9920-03G system (Hamamatsu Photonics) isused. Quantum yields and CIE coordinates are determined using thesoftware U6039-05 version 3.6.0.

Emission maxima are given in nm, quantum yields Φ in % and CIEcoordinates as x,y values. PLQY is determined using the followingprotocol:

-   -   1) Quality assurance: Anthracene in ethanol (known        concentration) is used as reference    -   2) Excitation wavelength: the absorption maximum of the organic        molecule is determined and the molecule is excited using this        wavelength    -   3) Measurement        -   Quantum yields are measured, for sample, of solutions or            films under nitrogen atmosphere. The yield is calculated            using the equation:

$\Phi_{PL} = {\frac{n_{photon},{{emi}ted}}{n_{photon},{absorbed}} = \frac{\int{{\frac{\lambda}{hc}\left\lbrack {{{Int}_{emitted}^{s\alpha mple}(\lambda)} - {In{t_{\alpha b{sorbed}}^{s\alpha mple}(\lambda)}}} \right\rbrack}d\lambda}}{\int{{\frac{\lambda}{hc}\left\lbrack {{In{t_{emitted}^{reference}(\lambda)}} - {In{t_{\alpha b{sorbed}}^{reference}(\lambda)}}} \right\rbrack}d\lambda}}}$

-   -   -   wherein n_(photon) denotes the photon count and Int. the            intensity.

Production and Characterization of Optoelectronic Devices

Optoelectronic devices, such as OLED devices, comprising organicmolecules according to the invention can be produced viavacuum-deposition methods. If a layer contains more than one compound,the weight-percentage of one or more compounds is given in %. The totalweight-percentage values amount to 100%, thus if a value is not given,the fraction of this compound equals to the difference between the givenvalues and 100%.

The not fully optimized OLEDs are characterized using standard methodsand measuring electroluminescence spectra, the external quantumefficiency (in %) in dependency on the intensity, calculated using thelight detected by the photodiode, and the current. The OLED devicelifetime is extracted from the change of the luminance during operationat constant current density. The LT50 value corresponds to the time,where the measured luminance decreased to 50% of the initial luminance,analogously LT80 corresponds to the time point, at which the measuredluminance decreased to 80% of the initial luminance, LT 95 to the timepoint, at which the measured luminance decreased to 95% of the initialluminance etc. Accelerated lifetime measurements are performed (e.g.applying increased current densities). Exemplarily LT80 values at 500cd/m² are determined using the following equation:

${LT}\; 80{\left( {500\frac{{cd}^{2}}{m^{2}}} \right) = {LT80\left( L_{0} \right)\left( \frac{L_{0}}{500\frac{{cd}^{2}}{m^{2}}} \right)^{1.6}}}$

wherein L₀ denotes the initial luminance at the applied current density.

The values correspond to the average of several pixels (typically two toeight), the standard deviation between these pixels is given.

HPLC-MS:

HPLC-MS spectroscopy is performed on a HPLC by Agilent (1100 series)with MS-detector (Thermo LTQ XL). A reverse phase column 4.6 mm×150 mm,particle size 5.0 μm from Waters (without pre-column) is used in theHPLC. The HPLC-MS measurements are performed at room temperature (rt)with the solvents acetonitrile, water and THF in the followingconcentrations:

solvent A: H₂O (90%) MeCN (10%)

solvent B: H₂O (10%) MeCN (90%)

-   -   THF

solvent C: (100%)

From a solution with a concentration of 0.5 mg/ml an injection volume of15 μL is taken for the measurements. The following gradient is used:

Flow rate time A B D [ml/min] [min] [%] [%] [%] 3 0 40 50 10 3 10 10 1575 3 16 10 15 75 3 16.01 40 50 10 3 20 40 50 10Ionisation of the probe is performed by APCI (atmospheric pressurechemical ionization).

Example 1

Example 1 was synthesized according to the general procedure forsynthesis, wherein 1-chloro-2-iodo-3-(phenylmethoxy)benzene (E1 and E2)and 4-amino-3,5-difluorobenzonitrile (E3) were used as reactants.

Additional examples of organic molecules of the invention

1. An organic molecule having a structure of Formula

wherein X is O or S; Y is O or S; R¹ is selected from the groupconsisting of: hydrogen, deuterium, C₁-C₅-alkyl, which is optionallysubstituted with one or more substituents R⁵; C₆-C₆₀-aryl, which isoptionally substituted with one or more substituents R⁵; andC₃-C₅₇-heteroaryl, which is optionally substituted with one or moresubstituents R⁵; R², R³, and R⁴ are independently from each otherselected from the group consisting of: hydrogen, deuterium,C₁-C₄₀-alkyl, which is optionally substituted with one or moresubstituents R⁵; C₁-C₄₀-alkoxyl, which is optionally substituted withone or more substituents R⁵; C₂-C₄₀-alkenyl, which is optionallysubstituted with one or more substituents R⁵; C₂-C₄₀-alkynyl, which isoptionally substituted with one or more substituents R⁵; C₆-C₆₀-aryl,which is optionally substituted with one or more substituents R⁵;C₃-C₅₇-heteroaryl, which is optionally substituted with one or moresubstituents R⁵; CN; CF₃; N(R⁵)₂; OR⁵, and Si(R⁵)₃; R^(I), R^(II),R^(III), R^(IV), R^(V) and R^(VI) is independently from each otherselected from the group consisting of: hydrogen, deuterium,C₁-C₄₀-alkyl, which is optionally substituted with one or moresubstituents R⁵; C₁-C₄₀-alkoxyl, which is optionally substituted withone or more substituents R⁵; C₂-C₄₀-alkenyl, which is optionallysubstituted with one or more substituents R⁵; C₂-C₄₀-alkynyl, which isoptionally substituted with one or more substituents R⁵; C₆-C₆₀-aryl,which is optionally substituted with one or more substituents R⁵;C₃₋C₅₇-heteroaryl, which is optionally substituted with one or moresubstituents R⁵; CN; CF₃; N(R⁵)₂; OR⁵, and Si(R⁵)₃; R⁵ is at eachoccurrence independently from another selected from the group consistingof: hydrogen, deuterium, OPh, CF₃, CN, F, C₁-C₅-alkyl, whereinoptionally one or more hydrogen atoms are independently from each othersubstituted by deuterium, CN, CF₃, or F; C₁-C₅-alkoxy, whereinoptionally one or more hydrogen atoms are independently from each othersubstituted by deuterium, CN, CF₃, or F; C₁-C₅-thioalkoxy, whereinoptionally one or more hydrogen atoms are independently from each othersubstituted by deuterium, CN, CF₃, or F; C₂-C₅-alkenyl, whereinoptionally one or more hydrogen atoms are independently from each othersubstituted by deuterium, CN, CF₃, or F; C₂-C₅-alkynyl, whereinoptionally one or more hydrogen atoms are independently from each othersubstituted by deuterium, CN, CF₃, or F; C₆-C₁₈-aryl, which isoptionally substituted with one or more C₁-C₅-alkyl substituents;C₃-C₁₇-heteroaryl, which is optionally substituted with one or moreC₁-C₅-alkyl substituents; N(C₆-C₁₈-aryl)₂, N(C₃-C₁₇-heteroaryl)₂; andN(C₃-C₁-heteroaryl)(C₆-C₁₈-aryl).
 2. The organic molecule according toclaim 1, wherein R¹, R², R³, R^(I), R^(II), R^(III), R^(IV), R^(V) andR^(VI) are independently from selected from the group consisting of:hydrogen, deuterium, halogen, Me, ^(i)Pr, ^(t)Bu, CN, CF₃, Ph, which isoptionally substituted with one or more substituents independently fromeach other selected from the group consisting of Me, ^(i)Pr, ^(t)Bu, CN,CF₃, and Ph, pyridinyl, which is optionally substituted with one or moresubstituents independently from each other selected from the groupconsisting of Me, ^(i)Pr, ^(t)Bu, CN, CF₃, and Ph, pyrimidinyl, which isoptionally substituted with one or more substituents independently fromeach other selected from the group consisting of Me, ^(i)Pr, ^(t)Bu, CN,CF₃, and Ph, carbazolyl, which is optionally substituted with one ormore substituents independently from each other selected from the groupconsisting of Me, ^(i)Pr, ^(t)Bu, CN, CF₃, and Ph, triazinyl, which isoptionally substituted with one or more substituents independently fromeach other selected from the group consisting of Me, ^(i)Pr, ^(t)Bu, CN,CF₃, and Ph, and N(Ph)₂.
 3. The organic molecule according to claim 1,wherein R², R⁴, R^(I), R^(II), R^(III), R^(V), and R^(VI) areindependently selected from the group consisting of: hydrogen,deuterium, halogen, Me, ^(i)Pr, ^(t)Bu, CN, CF₃, Ph, which is optionallysubstituted with one or more substituents independently from each otherselected from the group consisting of Me, ^(i)Pr, ^(t)Bu, CN, CF₃, andPh, pyridinyl, which is optionally substituted with one or moresubstituents independently from each other selected from the groupconsisting of Me, ^(i)Pr, ^(t)Bu, CN, CF₃, and Ph, pyrimidinyl, which isoptionally substituted with one or more substituents independently fromeach other selected from the group consisting of Me, ^(i)Pr, ^(t)Bu, CN,CF₃, and Ph, and triazinyl, which is optionally substituted with one ormore substituents independently from each other selected from the groupconsisting of Me, ^(i)Pr, ^(t)Bu, CN, CF₃, and Ph; and R³, R^(II), andR^(V) is independently from another selected from the group consistingof: hydrogen, deuterium, Me, ^(i)Pr, ^(t)Bu, Ph, which is optionallysubstituted with one or more substituents independently from each otherselected from the group consisting of Me, ^(i)Pr, ^(t)Bu, and Ph,carbazolyl, which is optionally substituted with one or moresubstituents independently from each other selected from the groupconsisting of Me, ^(i)Pr, ^(t)Bu, CN, CF₃, and Ph, and N(Ph)₂.
 4. Theorganic molecule according to claim 3, wherein R², R⁴, R^(I), R^(II),R^(III), R^(IV), and R^(VI) are independently selected from the groupconsisting of: hydrogen, deuterium, Me, ^(i)Pr, ^(t)Bu, CN, CF₃, and Ph,which is optionally substituted with one or more substituentsindependently from each other selected from the group consisting of Me,^(i)Pr, ^(t)Bu, CN, CF₃, and Ph; R³, R^(II) and R^(V) is independentlyfrom another selected from the group consisting of hydrogen, deuterium,Me, ^(i)Pr, ^(t)Bu, Ph, which is optionally substituted with one or moresubstituents independently from each other selected from the groupconsisting of Me, ^(i)Pr, ^(t)Bu, and Ph, carbazolyl, which isoptionally substituted with one or more substituents independently fromeach other selected from the group consisting of Me, ^(t)Bu, and Ph andN(Ph)₂.
 5. The organic molecule according to claim 1, wherein R¹ isC₆-C₃₀-aryl, which is optionally substituted with one or moresubstituents independently from each other selected from the groupconsisting of Me, ^(i)Pr, ^(t)Bu, CN, CF₃, and Ph.
 6. The organicmolecule according to claim 5, wherein R¹ is phenyl or mesityl.
 7. Theorganic molecule according to claim 1, comprising a structure of one ofFormulas II to XXI:

8.-13. (canceled)
 14. A composition comprising: (a) at least one organicmolecule according to claim 1 as an emitter and/or host; (b) one or moreemitter and/or host materials different from the at least one organicmolecule according to claim 1, and (c) optionally one or more dyesand/or one or more solvents.
 15. An optoelectronic device comprising theorganic molecule according to claim 1, wherein the optoelectronic deviceis an organic light-emitting diode, light-emitting electrochemical cell,organic light-emitting sensor, an organic diode, an organic solar cell,an organic transistor, an organic field-effect transistor, an organiclaser or a down-conversion element.
 16. The optoelectronic deviceaccording to claim 15, comprising: a substrate; an anode; a cathode,wherein the anode or the cathode is applied to the substrate; and atleast one light-emitting layer disposed between the anode and thecathode and which comprises the organic molecule.
 17. An optoelectronicdevice comprising the organic molecule according to claim 1, wherein theorganic molecule is one of a luminescent emitter, an electron transportmaterial, a hole injection material or a hole blocking material in theoptoelectronic device.
 18. The optoelectronic device according to claim17, wherein the optoelectronic device is an organic light-emittingdiode, light-emitting electrochemical cell, organic light-emittingsensor, an organic diode, an organic solar cell, an organic transistor,an organic field-effect transistor, an organic laser or adown-conversion element.
 19. An optoelectronic device comprising theorganic molecule according to claim 2, wherein the optoelectronic deviceis an organic light-emitting diode, light-emitting electrochemical cell,organic light-emitting sensor, an organic diode, an organic solar cell,an organic transistor, an organic field-effect transistor, an organiclaser or a down-conversion element.
 20. The optoelectronic deviceaccording to claim 19, comprising: a substrate; an anode; a cathode,wherein the anode or the cathode is applied to the substrate; and atleast one light-emitting layer disposed between the anode and thecathode and which comprises the organic molecule.
 21. An optoelectronicdevice comprising the organic molecule according to claim 2, wherein theorganic molecule is one of a luminescent emitter, an electron transportmaterial, a hole injection material or a hole blocking material in theoptoelectronic device.
 22. The optoelectronic device according to claim21, wherein the optoelectronic device is an organic light-emittingdiode, light-emitting electrochemical cell, organic light-emittingsensor, an organic diode, an organic solar cell, an organic transistor,an organic field-effect transistor, an organic laser or adown-conversion element.
 23. An optoelectronic device comprising thecomposition according to claim 14, wherein the optoelectronic device isan organic light-emitting diode, light-emitting electrochemical cell,organic light-emitting sensor, an organic diode, an organic solar cell,an organic transistor, an organic field-effect transistor, an organiclaser or a down-conversion element.
 24. The optoelectronic deviceaccording to claim 23, comprising: a substrate; an anode; a cathode,wherein the anode or the cathode is applied to the substrate; and atleast one light-emitting layer disposed between the anode and thecathode and which comprises the composition.
 25. A process for producingan optoelectronic device, comprising processing of the organic moleculeaccording to claim 1 by a vacuum evaporation method or from a solution.26. A process for producing an optoelectronic device, comprisingprocessing of the composition according to claim 14 by a vacuumevaporation method or from a solution.